Yohimbine (CHEM017527)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:26:07 UTC
Update Date2016-11-09 01:15:36 UTC
Accession NumberCHEM017527
Identification
Common NameYohimbine
ClassSmall Molecule
DescriptionA plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-YohimbineChEBI
(16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylic acid methyl esterChEBI
17alpha-Hydroxyyohimban-16alpha-carboxylic acid methyl esterChEBI
AphrodineChEBI
CorynineChEBI
JohimbinChEBI
QuebrachinChEBI
QuebrachineChEBI
Yohimbic acid methyl esterChEBI
YohimbinChEBI
(16a,17a)-17-Hydroxyyohimban-16-carboxylate methyl esterGenerator
(16a,17a)-17-Hydroxyyohimban-16-carboxylic acid methyl esterGenerator
(16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylate methyl esterGenerator
(16Α,17α)-17-hydroxyyohimban-16-carboxylate methyl esterGenerator
(16Α,17α)-17-hydroxyyohimban-16-carboxylic acid methyl esterGenerator
17a-Hydroxyyohimban-16a-carboxylate methyl esterGenerator
17a-Hydroxyyohimban-16a-carboxylic acid methyl esterGenerator
17alpha-Hydroxyyohimban-16alpha-carboxylate methyl esterGenerator
17Α-hydroxyyohimban-16α-carboxylate methyl esterGenerator
17Α-hydroxyyohimban-16α-carboxylic acid methyl esterGenerator
Yohimbate methyl esterGenerator
AphrodyneHMDB
Aventis brand OF yohimbine hydrochlorideHMDB
Solvay brand OF yohimbine hydrochlorideHMDB
Yohimbine hydrochlorideHMDB
Aphrodine hydrochlorideHMDB
Hydrochloride, yohimbineHMDB
PlurivironHMDB
RauwolscineHMDB
Palisades brand OF yohimbine hydrochlorideHMDB
Star brand OF yohimbine hydrochlorideHMDB
StegroPharm brand OF yohimbine hydrochlorideHMDB
Tartrate, corynanthineHMDB
CorynanthineHMDB
Corynanthine tartrateHMDB
Glenwood brand OF yohimbine hydrochlorideHMDB
Hydrochloride, aphrodineHMDB
Kramer brand OF yohimbine hydrochlorideHMDB
RauhimbineHMDB
YoconHMDB
Yohimbin spiegelHMDB
Yohimbine houdéHMDB
YohimexHMDB
Chemical FormulaC21H26N2O3
Average Molecular Mass354.443 g/mol
Monoisotopic Mass354.194 g/mol
CAS Registry Number146-48-5
IUPAC Namemethyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate
Traditional Nameyohimbine
SMILES[H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2
InChI IdentifierInChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChI KeyBLGXFZZNTVWLAY-SCYLSFHTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassYohimbine alkaloids
Sub ClassNot Available
Direct ParentYohimbine alkaloids
Alternative Parents
Substituents
  • Yohimbine
  • Corynanthean skeleton
  • Yohimbine alkaloid
  • Beta-carboline
  • Pyridoindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Beta-hydroxy acid
  • Hydroxy acid
  • Benzenoid
  • Piperidine
  • Heteroaromatic compound
  • Methyl ester
  • Cyclic alcohol
  • Pyrrole
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxylic acid ester
  • Tertiary amine
  • Secondary alcohol
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxide
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP2.36ALOGPS
logP2.1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)7.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.63 m³·mol⁻¹ChemAxon
Polarizability40.22 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-008i-0396000000-43448cca1e1ad4343ac0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xs-2139200000-8288a21cfcdae82fc694Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-3921000000-e28dd8692e2b8dd63330Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0019000000-98fd50566f845231fbedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0129000000-49a3b77851cb2f327e51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ffx-0891000000-1297a98bf2d980f32361Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-6448f2e7be3b7fa35128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-a436855e9ddc5d8e061eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07ef-3956000000-386e3fa9fb16f1a30cf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-b3d998cb3c47c9700660Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-42b2cee0514145bdbc16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002g-0695000000-7eacdb4b3fbff0521dcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-1bc1d16b561be98b6dbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0095000000-d9723526ae361fda41c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-0192000000-a13fb9eefdc725558673Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01392
HMDB IDHMDB0015464
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001789
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkYohimbine
Chemspider ID8622
ChEBI ID10093
PubChem Compound ID8969
Kegg Compound IDC09256
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available